WSJ did an interview with Ben Fried, Google’s CIO, recently on how internal IT tools impact organisational culture. Several pertinent points were covered, and here are some that struck me, along with my 2 cents.

CIOs need to understand the cultural thing—they define the culture of their company by the technology they give to their employees. So much of the culture stems from how we work.

The statement of fact that culture is an outcome of how we work is not recognised enough. On one end management often wishes their teams were more nimble in their execution but do not provide the support structure and the tools necessary to accomplish it. In balancing between predictability and speed, traditional organisations often choose predictability. Of course, few modern enterprises like Netflix, Amazon and Google seem to have mastered being predictably nimble and it shows in the kind of tools they have built and even open-sourced.

The right thing to do is to help people be as productive as possible, and the way to do that is…to understand the toolset that people who come to work every day know how to use…and want to use. To the best of your ability, you need to give them that toolset. When you do that, it creates a completely different organizational culture.

When people feel like they aren’t part of the decision-making process, they feel treated like children, they feel resentful and you find examples of belligerent compliance. When people feel like they have had a say, like they have been empowered, you get collaboration and cooperation.

Could not agree with this more than I do now. Winning organisations aim to reduce friction, and tool choice is such a critical part of enabling people to executing on business goals. Just remembering SharePoint intranet portal gives me shudders! Or how many hoops we had to go through to get a space on the corporate data centre, as compared to situation in a start-up where virtual instances are made live on-demand on AWS in a couple of minutes.

So how do these organisations support the technology diversity that emerges?

We can’t afford to have technology support where there are cookbooks and rules and every possible change is documented in advance. The people we hire to do support are more like systems administrators in another company. The first responder closes the ticket over 90% of the time in my organization.

That completely nails it. Instead of hiring the resource you can get and having them follow documented processes, they hire people skilled enough to be systems administrators and have them address complexities that arise. There is minimal documentation but the skills make up for this deficiency! Am sure this approach would be shot down in a traditional setup. Of course it would cost more to hire such a person but the agility that results more than makes up for the cost.

On a side note, in taking our CollabLayer product to market I have noticed this culture aspect cropping up. Traditional organisations, with investments in tools like SharePoint Portal, find it a culture shock to have our system bubble up semantic connections implicit within their content. Their first question often is whether we are secure! Our system obeys security rules in highlighting semantic connections in content but still older cultures take a little time adjusting to increased transparency.

As a contrast, smaller teams who need to accomplish more with less people love our approach to managing content & conversations around them and insight discovery. Guess it boils down to what Ben mentions, culture does stem from how we work, and tool choice is a factor in this equation.

Check the whole interview with Ben Fried, worth mulling over whether your organisation can benefit from such an approach.

Whatever it may otherwise lack, a Startup is blessed with an abundance of unknowns. What is the product? Who is the customer? What is the value proposition? How will you sell? At what price point? The utterly simple yet immensely vexing answer to all these questions is “We don’t know fully”. Of course I jest, but only a little. This is the Sphinx posing its riddles.

In a startup, everything and nothing is open for exploration. Sounds like one of those contradictory Zen statements but believe me there is nothing remotely calm or enlightening about this state.

When friends or ex-colleagues try to comprehend our proposition, there is always a glint of sympathy in their eyes. I almost hear them thinking, “How misguided could you get?”, “Can’t you focus on key features?”, “Where is your execution plan?”, “Are you making money?”, “I did a MVP last weekend, what takes you so much time?” and so on.

Or when arguing about evolving the product in a specific direction with my team, I always feel the tension. Features change, evolve, mutate like a precocious two year old’s imagination. What was to be a journey to India, is possibly leading us to an entirely different continent, while making us feel lost in a wide sea of unknowns.

How do I deal with it? Well, the unknown to me is always a possibility. Something to be unwrapped and explored. As my Guru Sri Aurobindo, says in an aphorism:

The sense of impossibility is the beginning of all possibilities.

To confront impossibility is to stand firm in front of the Sphinx posing its riddles. You stand and answer its questions. The more it questions, the deeper you dig and answer. If you give up, the Sphinx wins.

Whether its rewriting a feature you removed few weeks back. Or venturing into a technical area you know very little about. Or doing a pre-sales call. Or dealing with a hundred less than ideal situations at work and elsewhere. That is the Sphinx presenting itself to you.

The Sphinx is not a statue posing its impossibility on a ocean of sand far far away. The Sphinx is a customized version of impossibility created just for you. To everyone else the riddle is plain, simple and they might think you naive, perhaps even that you are stupid. It could be true too. But this is your impossibility. Your personal Tour De France. Your Everest. This is Xerxes confronting you with his Persian might.

The Sphinx demands answers. The unknown demands exploration. Tenacity is what you must live and breathe. To wake up and greet your unknowns. To welcome them one by one. To dissect and get into and get around them. To do everything but giving up.

And then you might hear one day, as I did earlier today, “This has promise”, in reference to our product. There is still long way to go but hey, even the imaginary sound of seagulls is music to my ears now.

Am sure this is familiar to anyone in startup mode. Endless possibilities, danger of losing focus at every turn and no sight of a home. Homer, poet of Ancient Greece, shows how Odysseus, the hero of Odyssey, maintains his focus.

Situation

Odysseus is trying to get home. His immediate problem is to navigate along with his men beyond the Sirens, maidens of beauty and heart wrenching songs. Those who heard the Sirens abandoned prudence and rushed to rocky coasts.

Solution?

Odysseus has his team’s ears blocked with beeswax, preventing them from hearing the Siren’s song. A song of unbearable longing that lures sailors, only to dash their ships to doom on treacherous seas. Odysseus is curious to hear the song, but is pragmatic enough not to trust himself, hence has himself tied to the ship’s mast. So the team is not distracted and he is tied to his purpose, literally in this case.

Thus, the team row their way past the Sirens. Odysseus survives the Siren’s call to doom by being firm in his commitment and a little foresight.

So, if you are working on your startup, be open to possibilities, both benign and malicious. But commit yourself to a schedule, a plan or your original vision. Do not heed every call to new opportunities and change course. Trust your intuition and keep moving. Beware unbelievably nice possibilities. And keep yourselves focussed on execution.

Makes sense?

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What did we do with such focus? CollabLayer is what we did. A cloud-based collaboration tool that enables collaborative content consumption, discussions in context and rapid discovery of insight. If your work involves reviewing, sharing and discussing digital content with a team, you should really check it out. Free during beta and you can always take your data back. Learn about motivations behind CollabLayer. Or head here to Signup.

Digg is dead. Digg’s failure was a chance for bloggers to speculate about Digg itself and what makes startups fail and rise up.

There were the usual condescending views on what happened to Digg. See picture below.

In case you did not get the joke, here is the actual cover published many years ago.

There were positive takes too, for example here is one from Sarah Lacy:

The lesson from Digg is crucial as Silicon Valley’s ecosystem has made it easier and easier to start a company. It’s that a great product is necessary but not nearly enough. Building a real company is harder, and it takes execution and leadership.

And Sarah ends the article with this:

There will be haters on this post. And that’s fine. But the people who write checks in the Valley have respect for what Digg built, whether the founders fell short or not. Smart people will always want to back these guys– as Mike Maples said on Ask a VC last week– and people like Arrington and me will root for them again.

Context of Failure

In my understanding there is a specific context in which the sentiment “failure is acceptable” occurs. This context is driven by three factors.

First, the economic drivers of society have changed from being manufacturing oriented to one driven by information and software. Software products are not typically capital intensive, besides Moore’s Law ensures more CPU power being available for less cost. So software companies are born, grow and mature at a much faster rate than those that manufacture things.

Second, most major economies are globalized, coupled with spread of internet and internet based services makes an unimaginable amount of competition possible. The key here is that location is not an impediment to build and sell software. As long as connectivity exists, any service can theoretically be served anywhere. Theoretically because there are laws around what can be sold from and to in each nation. But in principle location is not a hard barrier for digital services.

Third, increasing complexity of societies driven by change in demographics of nations, the migration from rural areas into cities, availability of cheap communication devices, affordable internet connectivity and other factors drive an inordinate rate of change and new perspectives that leave little room for certainty.

Consequence

With the above three factors influencing our context, it is easy to work out why investors and entrepreneurs take the stance that “failure is acceptable“. Basically very few have any certainty on what product or service will succeed in the marketplace. A product that succeeds in the US, does not even start in Brazil or India or China. There are no clear answers.

The option to not failing seems to be to sit tight, which certainly is no option for dreamers and builders. Besides in software related services the life-span of vetting a product is quite short. Unlike manufacturing a car where it takes a few years to build one and then test to see if it succeeds, a prototype software product can be done in as few as handful of weeks to get feedback from potential customers.

So a couple of years spent building a software product that has failed is no big deal, the experience of having executed idea still remains valuable. These lessons learnt from failure and the endurance built up in execution can be reused. The VCs and entrepreneurs have thought through these dynamics, leading to insight that failure does not kill and one can always try again.

Bottom line, execution builds competency regardless of outcome.

Is it just a fashion?

I also think, this is no ephemeral trend..this is a deeper perspective of what makes work essential to us as humans. Beyond its ability to put food on the table, work infuses meaning to many of us and without that ability to leave markers around many would be unhappy. But here I digress into philosophical territory and will have to stop I guess! What do you think? What makes failure acceptable, at least in the technology industry?

Warning! If your heart and mind are immune to poetry, and its ability to communicate complex ideas and feeling, please stop reading and come back later!

Silence yourself, really..whatever it is you are doing now, just let it all go. Done? Okay, here is a little poem that gives a hint of how it feels to launch a startup and create a product. As I said, if you have never felt poetry hit your heart, this might not work. Anyway, pay attention and read it now.

How to build an Owl

Decide you must.

Develop deep respect

for feather, bone, claw.

Place your trembling thumb

where the heart will be:

for one hundred hours watch

so you will know

where to put the first feather.

Stay awake forever.

When the bird takes shape

gently pry open its beak

and whisper into it: mouse.

Let it go.

That gentlemen is how it is. There is indeed a science and reasoning behind everything but a large part of it feels like a mystery. You could have been an Oracle in a temple of Delphi trying to figure out what the spirits are trying to say!

If there is just one aspect I have to highlight as most terrifying, then it would be figuring out what to build. That single question is like every imaginary evil figure come together just to mess with you. You think that is easy? Ah, I thought the same too. Let me clarify. This is like the Mule, Zombies, Satan, Voldemort and..and Sauron coming together..they all shake hands just to mess with you..exclusively. That said, it is an amazing ride and sure beats playing politics and putting up with mediocrity.

I stepped outside the door last week of August 2011. After 15 odd years of relentless running I had the opportunity to step back and consider the runner, the running and the race.

“It’s a dangerous business, Frodo, going out your door. You step onto the road, and if you don’t keep your feet, there’s no knowing where you might be swept off to.” – J.R.R. Tolkien, The Lord of the Rings

Am yet to be ‘swept off’ but the journey so far has been exhilarating, surprising and challenging. Below I share a little of what I have realized and learnt so far.

Context changes everything. Including what you know of yourself and others.

What remains after labels are stripped away is character.

Not every relationship sprouts.

Serendipity does happen!

Full-time employment or startup is a question of which challenges you wish to take on.

Power unveils character.

There is generosity in unexpected places, seek it.

Conventional wisdom on anything breaks down at the fine-print.

Complete freedom is harder to handle than it appears. Empathize with men who elect to be constrained.

What you do when you can do anything is driven by character.

All considered, I feel I should have walked out the door sooner. And yes I do have things other than aphorisms to talk about 🙂 I shall do another update on my startup, progress so far and thoughts on next steps.

And am curious, what did you learn last year about the world and yourself?

I have had phenomenal luck in getting to work with some world class people for most of my career. But the good run ended last year, when a majority of my bets on the people front failed. In hindsight I think it was about expectation setting and lack of shared understanding in what it means to work in a startup like environment, specifically within the context of the new people who came on board.

I have attempted to provide my view of what factors are involved in working for a startup or startup-like environment. Obviously I have not covered everything and the factors listed below are relevant to resources I have worked with, or attempted to work with, in Bangalore, India. So some of these factors might not be relevant to your environment.

Technical Skills

This is the foundation upon which all others take their place. Not necessarily all technical but means skills relevant to the function one performs.

If you are an architect, lead or developer then to have skills commensurate with your experience. To think through a problem with rigor and completeness. To bring the same attention to naming a function or class as you would in drawing a grand architectural overview. Not just the syntax but to know the why and the how. Because real-world problems don’t come advertising the solution. You got to investigate, probe and analyze. You need to build a hypothesis and test it. You need an arsenal of techniques to understand and solve the problem.

To think broad during problem analysis and to think deep during execution. To balance form and function. To think of various costs(development, testing, maintaining, supporting etc.) when evaluating possible solutions.

Ability to learn a new tool quickly to solve a problem. To understand that an architecture evolves over a period of time, that nothing worth its salt is ever simple.

Ownership

To own something. Be it a feature, a module or the whole product. To own it in its entirety, from definition to rollout. Own it enough to shepherd it through the challenges of surviving reality. To feel every criticism of your creation as a barb in your being. To cherish every small win as your own.

An attitude and state that is the very antithesis of product efforts at most large organizations and especially service organizations, where one owns a small sliver and spends a life-time becoming an expert in it. An attitude that does not play by the rule book, that demands realization today. An attitude that takes pride in crafting something to be remembered by.

Multi-tasking/Context Shifting

The ability to juggle multiple work-streams, in sequence most of the times and sometimes in parallel. And yet not lose productivity or rigor in execution. One needs to be in the zone to hit the high mode of super productivity, but a startup environment has demands that will not wait or cannot be delegated because there are no people to delegate to.

Being annoyed or saying you cannot deal with context shifts is not an option. You deal with it and survive to battle another day.

Commercial Savviness

Developers usually have little sense of commercial considerations. Sales folks are slightly better at it, though their preferences are colored by the commission they can potentially make. In a startup environment where one person can play product manager, quality assurance/tester, sales and marketing roles, sometimes all in the same day. As a star SEO consultant in Bangalore once said to me, ” It is essential every person in the organization brings this commercial savviness to the table. Every decision has a cost and influences what options are available in the future”.

Perseverance

When bringing out a product your first set of customers would, almost as a rule, gift you with a barrage of criticism. Especially if your product challenges any of the traditional mindsets adopted in performing a specific function.

A demo to a key large customer would fail because someone updated a piece code a couple of hours back. You would spend months coming close to sign off and the customer would walk away without explaining why. Or a client would be willing to sign only if you had features X, Y and Z, and give them a significant discount because they are willing to go with you.

Or, your new hire does not get the urgency of what you need, does not believe in what you do and spreads bad blood within the team, does not turn out to be the rock star you expected them to be, only provides arm-chair criticism of your strategy without providing a credible alternative. A developer you depend on to deliver a key feature leaves the firm.

You get the drift. Challenges on a daily basis is the norm. Yield and there will be no end until your vision is flattened. Trick is to persevere until the last man standing gets the job done.

Vision

This is the ability to look beyond the obvious. To consider approaches that are unconventional. Articulate needs the customer does not know about yet.

Not everyone in a startup needs this ability, most need to just execute well. But without this ability to see what is not there yet one lacks the key to understand a startup environment. Without the ability to be irrationally passionate about a vision, one does not get the rush of being in a startup. One just sees a bunch of people running about, has no clue what is so special about this effort and leaves disappointed.

Empathy

Finally empathy. It is hard to run a marathon every waking day. It just burns out people. Work-life balance, workplace diversity all come in once there is revenue and a org structure to support the product. Until then you push yourself and your team to the brink of their abilities.

But for those who attempt it, treat them with empathy. It does not matter who. From the junior most team member to the guy driving the show, each is a human with all the strengths and insecurities that make up many of us. Lend each other a hand. Each have their highs and lows. Take a balanced perspective.

Summary

In summary, some people are not just cut out for a startup environment. They might not be skilled enough, might be suited to lesser efforts, cannot offer the dedication required or just have different goals. And that is okay. They should be humble enough to accept it and move on, and you should be understanding enough to let them go amicably.

Because the Buddha did not ordain everyone who crossed his path, nor did Christ pick every passerby as a disciple, it is just the way it is. Some are destined and some are not 🙂

And for those who join the ride, reward dedication. Be fiercely loyal to the team that has trusted you. Believe in your vision. Craft beautiful things. Cherish every victory. Fight a good fight. And become the story a handful share with each other in the future.

[Note: Apologies for the lack of structure. I just had to get this out. Comments/Feedback appreciated.]

Fred Wilson of A VC captures the details of being in a trough after the initial high of launching a product. I quote a pertinent passage below.

The ugly adolescent stage is when you’ve built the product and are now building the business. It is when the team grows beyond the intial founding group and not everyone is getting along so well. It is when you are no longer that "bright shiny thing" that everyone wants to talk about. It is when your users are complaining that the service is not reliable or they hate that new feature or interface. It is when you have to figure out how to make money and get profitable. It is when the founder starts to wonder whether this CEO thing is for him or her. It is when you need that next round of financing and it isn’t so easy to raise this time.

Having conceived and launched a product this year I can utterly vouch for the generalities and specifics of what Fred mentions in the post.

Of course I have done this within the framework of the current firm I work for but it does not change the messiness in any fashion. In fact, if anything, it only gets more difficult because not only are you dealing with external competitors, enterprise customers with their glacial decision making speeds, looking for people who have the rigor to build a product but also have to deal with internal politics and organizational bureaucracy. And that can severely test anybody.

So far I have lacked a framework to understand what the heck is happening in my own context. Fred’s post has helped clarify that this is just another phase that has to be overcome and others before me have done the same.

Dharmesh Shah on his startup focused blog talks about partnerships. For all of you who are contemplating startups, or working for organizations in merger/takeover talks, this is a must read.

A sample quote: PR Glow Lasts A Day, Lock-In Lasts Longer

The other points don’t hit you in the gut like the one above but are equally, if not more, valuable. I have seen the 4th point around what each company loses in a partnership play out.

The previous company I used to work for was a premium financial services consulting firm. With a set of blue chip clients, access to the C-level folks in the financial industry and consulting rates any services company would kill for it was a pleasure to work there. Not to say it was employee heaven though, shit happened but there was so much positive vibe and work happening that people generally got by without bitching too much.

And then they entered into a merger agreement with a much larger company. Right from the word go, regardless of what spin was attached to the partnership, it seemed doomed.

It has been 18+ months since I moved from the company and all of what I hear does nothing to make me want to go back. The larger firm brought as much strategic thinking to the table as a money lender would, was akin to a machine shop floor in its functioning, efficient but no finesse. The smaller firm thrived on personal relationships, consulting deals won through intellectual rigor, contacts and old fashioned ear to the ground.

This was chalk and cheese in hindsight. But guess what, the larger organization barely skipped a beat. The smaller organization though got ripped, its value proposition gone and its best people jumped ship.

The most valuable lessons for me in this, as a humble foot soldier on the ground, was this –

Balance sheets don’t tell the whole story – Not all aspects impacting a potential partnership can be deciphered through balance sheets and the counting beads of its accountants. Interact with the people at middle-management levels. This is typically hard to do when there is a blanket ban on talking to anyone but the official representatives on either side. But with so much of social media stuff happening, especially with blogs, facebook, twitter etc it should not be hard to get a sense of how the people at these levels think, how they work etc.

Strategy is top-down, execution is bottom-up – It is not enough if the C-level folks want the entities to merge, share infrastructure and gain operational efficiencies. Buy-in from the team on the ground is crucial. Or your ability to execute is going to be hampered. Like it or not a hundred processes that encodes the knowledge of your best people is useless. Unless you are a manufacturing outfit who will not change what you do for 10+years.

Distrust yes masters – Do your trusted lieutenants agree with whatever you do? If so, fire them now. You do not have to share your thoughts with those who always agree with you. Get contrary view points. Also grow enough to know an opinion is not the person. Not directly relevant to any merger/partnership process but very necessary because the more number of heads spinning out perspectives the better your chance you have at making this work.

Think very hard on the motivations of the other party – This one should be obvious 🙂